Hydroxyamine hydrochloride → 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime

HRID 2409011노트

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HRID 2409011 반응식
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl.[NH2:24][OH:25].CC([O-])=O.[Na+]>CO>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:24][OH:25])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

참가 물질

5

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HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898211-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone

생성물 1

HCID 1364090991-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime수율 97.6%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

To a mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone (1.32 g, 4.2 mmol) in MeOH (50 mL) at RT was added hydroxylamine hydrochloride (877 mg, 12.61 mmol) followed by NaOAc (3.45 g, 42.0 mmol). The reaction mixture was stirred at 80° C. for 1 h then concentrated tinder reduced pressure. Water (100 mL) was added to the reaction mixture, and the mixture extracted with EtOAc (50 mL×3). The combined organic layers were concentrated under reduced pressure to afford 1.35 g (97.6%) of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime as yellow solid: MS (ESI) m/z: 320.1 [M+1]+.

후처리

  1. concentrationthen concentrated tinder reduced pressure
  2. additionWater (100 mL) was added to the reaction mixture
  3. extractionthe mixture extracted with EtOAc (50 mL×3)
  4. concentrationThe combined organic layers were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-823c9862ff26494195853edf6d603314
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815877B2

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